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Novel Triterpene-Glycosides As Sweeteners Or Sweetener Enhancer

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Novel Triterpene-Glycosides As Sweeteners Or Sweetener Enhancer (19) TZZ¥Z_ _T (11) EP 3 501 296 A1 (12) EUROPEAN PATENT APPLICATION (43) Date of publication: (51) Int Cl.: 26.06.2019 Bulletin 2019/26 A23L 27/30 (2016.01) C07J 17/00 (2006.01) (21) Application number: 17210082.8 (22) Date of filing: 22.12.2017 (84) Designated Contracting States: • Kluge, Grit AL AT BE BG CH CY CZ DE DK EE ES FI FR GB 14959 Trebbin (DE) GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO • Jakupovic, Sven PL PT RO RS SE SI SK SM TR 13591 Berlin (DE) Designated Extension States: •Hetterling,Gregor BA ME 12057 Berlin (DE) Designated Validation States: • Tsichrintzi, Fotini MA MD TN 10707 Berlin (DE) (71) Applicant: Analyticon Discovery GmbH (74) Representative: Fabry, Bernd 14473 Potsdam (DE) IP2 Patentanwalts GmbH Schlossstrasse 523 (72) Inventors: 41238 Mönchengladbach (DE) • Dr. Siems, Karsten 14552 Michendorf (DE) (54) NOVEL TRITERPENE-GLYCOSIDES AS SWEETENERS OR SWEETENER ENHANCER (57) Suggested are triiterpene-glycoside com- pounds, which are obtainable by the extraction of Gynos- temma pentaphyllum which are useful as a sweetener or sweet taste enhancer in preparations and compositions, especially oral edible compositions. EP 3 501 296 A1 Printed by Jouve, 75001 PARIS (FR) EP 3 501 296 A1 Description FIELD OF INVENTION 5 [0001] The invention relates to novel triterpene-glycoside compounds, which are obtainable by the extraction of Gy- nostemma pentaphyllum and its physiologically acceptable salts which are useful as a sweetener or sweetener enhancer in preparations and compositions, especially oral edible compositions. STATE OF THE ART 10 [0002] Sweetness is one of the primary taste and cravings of both animals and humans. The universal use of naturally occurring and synthetic sweeteners to satisfy this natural craving has not been met without its accompanying physiological disadvantages, e.g. obesity, nutritional imbalance and dental decay. To overcome these unwanted disadvantages con- siderable research efforts and expenditures have been made to develop alternative compounds, e.g. as substitute for 15 the naturally occurring sweeteners or synthetic sweeteners which have no food value and are free of caloric input. While these artificial sweeteners enjoyed a wide use, and fulfilled the requirements of a sweet taste with no food value, and could be used without providing calories or damaging teeth, they were frequently found to possess inherent disadvantages that prevented their use for their intended purpose, e.g. because of their toxicity (p-ethoxyphenylurea) or chromosome damage and bladder trouble (sodium cyclamate). Thus, these sweeteners could not be safely recommended for use as 20 a sweetener and are apparently unacceptable for consumption. Saccharin compounds are also commonly used as artificial sweeteners, since cyclamates have been come under governmental restrictions. Although saccharin compounds possess sweetness characteristics, they are undesirable as the sole sweetening agent in most food and beverage compositions because of the lingering bitter aftertaste perceived by most users. While saccharin and the cyclamates have been in common use as artificial sweetening agents for a number of years, there has been more recently discovered 25 a series of new artificial sweeteners. [0003] For example US 3,087,821 (GENTILI ET AL) teaches the use of various dihydrochalcones having sugar sub- stituents (dihydrochalcones glycosides) as sweetening agents. All sweet dihydrochalkones have a licorice like aftertaste and linger in the mouth for some time. [0004] Siraitia grosvenori (Luo han guo), a member of the Cucurbitaceae family, is a plant native to some regions of 30 southern Asia and China. The sweet taste of fruits of luo han guo mainly comes from triterpene glycosides generally known as mogrosides. There are a number of mogrosides identified in luo han guo but generally mogroside V (CAS No: 88901-36-4)has the highest concentrationcompared toothers (Table1). Mogrol glycosides have the same core molecule- mogrol or oxo-mogrol and differ from each other by number and type of glycosidic residues bonded to mogrol or oxo- mogrol molecules [see US 2012/0059071, Kasai et al. AGRIC BIOL CHEM (1989), p 3347-3349; Matsumoto et. al. 35 CHEM PHARM BULL (1990) p 2030-2032.] Several mogrosides taste very sweet, often >100x sweeter than sucrose (EP 3099186 A2 , ANALYTICON DISCOVERY), including the major triterpene glycoside of Siraitia grosvenori, mogroside V, and its isomer iso-mogroside V (US 20110027413), but all of them have a certain bitter aftertaste. [0005] Leaves of Stevia rebaudiana are well known for its sweet taste due to its content of sweet diterpene glycosides. One of the major sweet compounds from stevia, Rebaudioside A, is approved as natural sweetener in US (since 2008) 40 und EU (since 2011). Apart from its sweet taste, all sweeteners from stevia have a slower onset and longer duration than that of sugar, and a bitter or licorice-like aftertaste at high concentrations [Lemus-Mondaca et al. FOOD CHEM 132 (2012) p 1121-1132]. [0006] Another example is EP 2529633 A1 (SYMRISE), which relates to triterpenes and triterpene glycosides and/or physiologically acceptable salts thereof. The triterpenes are, preferably naturally occurring triterpenes and triterpene 45 glycosidesfrom Mycetiabalansae, for generating asweet impressionin an orally consumableformulation or forreinforcing the sweet impression of an orally consumable formulation. These triterpene-glycosides differ in structure from the trit- erpenes claimed in the present invention. [0007] Gynostemma pentaphyllum is traditionally used as a natural sweetening agent in China. At least 85 triterpene glycosides were isolated from G. pentaphyllum, but only Gypenoside XX is known for its sweet taste (KINGHORN et 50 al., Terpenoid Glycoside Sweeteners in Natural Occurring Glycosides: Chemistry, Distribution and Biological Properties. John Wiley and Sons. Chichester, UK, 1999, p. 399-429.) [0008] Accordingly, it is a primary object of the present invention to provide novel sweetener compounds and its physiologically acceptable salts, which have a positive sweet benefit in food and oral compositions. In particular, the object was to provide sweetener compounds which are capable to provide sweetness to consumable compositions in 55 a way, that the balance between the degree of sweetness and the amount which has to be administered to obtain a sweet effect is comparable low, to overcome the aforesaid disadvantages associated with the prior art sweetener. It is another object of the present invention to provide sweetener compounds without astringent or bitter-taste aftertaste. The sweetener compounds to be specified should be toxicologically safe, effective already at relatively low concentrations, 2 EP 3 501 296 A1 well tolerated by the digestion, stable (in particular in normal cosmetic and/or pharmaceutical formulations), and easy to formulate and economical to produce. DESCRIPTION OF THE INVENTION 5 [0009] Object of the present invention is a sweetener composition comprising or consisting of at least one compound of general formula (I) 10 15 20 25 30 wherein R1, R1a and R1b are independent from each other and represent OH, OGlucose, or OXylose, or OGalaktose, or OAra- binose R2 is one of the following structures 35 40 45 50 with A1, A2 and A3 are independent from each other and represent H, OH, OOH, or OMe and B1 and B2 are independent from each other and represent H, OH, OOH, OMe, or O 55 and the dotted line means a single or a double bond. [0010] In the course of extensive studies on sweeteners, the present inventors succeeded in the isolation of novel sweetener compounds of formula (I) and found that these sweetener compounds of formula (I) show astonishingly good 3 EP 3 501 296 A1 and strong sweetness when compared with that of sucrose. PREFERRED COMPOUNDS 5 [0011] Of particular interest are the compounds of Formula (I) identified as: Compound A (NP-019652) [0012] 10 15 20 25 Compound B (NP-019654) 30 [0013] 35 40 45 50 Compound C (NP-019869) 55 [0014] 4 EP 3 501 296 A1 5 10 15 20 Compound D (NP-019870) 25 [0015] 30 35 40 45 Compound E (NP-019871) 50 [0016] 55 5 EP 3 501 296 A1 5 10 15 20 Compound F (NP-022163) [0017] 25 30 35 40 45 Compound G (NP-022167) [0018] 50 55 6 EP 3 501 296 A1 5 10 15 20 Compound H (NP-021249) 25 [0019] 30 35 40 45 Compound I (NP-021250) 50 [0020] 55 7 EP 3 501 296 A1 5 10 15 20 25 Compound J (NP-021251) [0021] 30 35 40 45 50 Compound K (NP-021252) [0022] 55 8 EP 3 501 296 A1 5 10 15 20 Compound L (NP-021253) 25 [0023] 30 35 40 45 EXTRACTS 50 [0024] Another object of the present invention refers to an extract comprising one or more of a compound of formula (I) obtainable by aqueous and/or alcoholic extraction of the plant Gynostemma pentaphyllum. Particularly preferred are extracts prepared from the leaves of G. pentaphyllum. 55 EXTRACTION PROCESS [0025] The extracts according to the present invention may be prepared by methods known per se, i.e. for example by aqueous, alcoholic or aqueous/alcoholic extraction of the plants or parts thereof. Suitable extraction processes are 9 EP 3 501 296 A1 any conventional extraction processes, such as maceration, re-maceration, digestion, agitation maceration, vortex ex- traction, ultrasonic extraction, counter current extraction, percolation, re-percolation, evacolation (extraction under re- duced pressure), diacolation and solid/liquid extraction under continuous reflux. Percolation is advantageous for industrial use. 5 [0026] The plant materials that are useful for obtaining the abstracts may include parts of the whole plant selected from the group consisting of blossoms, fruits, buds, roots, seeds and/or leaves or the whole plant itself. Leaves, however, are preferably used as the starting material and may be mechanically size-reduced before the extraction process. Any size reduction methods known to the expert, for example freeze grinding, may be used.
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